Pyridine → 3-Azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one

HRID 1856064Notes

Reaction equation

HRID 1856064 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=O.[N:14]([CH:17]1[CH:20](CCO)[NH:19][C:18]1=[O:24])=[N+:15]=[N-:16].N1C=CC=CC=1>C(Cl)Cl>[N:14]([CH:17]1[CH:20]([CH2:2][CH2:3][O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[NH:19][C:18]1=[O:24])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 155923893-Azido-4-(2-hydroxyethyl)-2-azetidinone

Product 1

HCID 543317643-Azido-4-(2-trifluoroacetoxyethyl)azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (0.2 mol) is added dropwise to an ice-cold, stirred solution of 3-azido-4-(2-hydroxyethyl)-azetidin-2-one (0.2 mol) and pyridine (0.21 mol) in methylene chloride (200 ml). The solution is stirred for 15 more min. at room temperature, then washed with water, dried with magnesium sulfate, and filtered. Evaporation of the methylene chloride under vacuum leaves 3-azido-4-(2-trifluoroacetoxyethyl)-azetidin-2-one.

Workup

  1. washat room temperature, then washed with water
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customEvaporation of the methylene chloride under vacuum

Sources & evidence

ORD record
ord-fcf150b556c84c8cbcc19bb3c44ee196
Source dataset
uspto-grants-1980_08
Patent number
US04217453

Reaction notes

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